Non-conjugated polymeric perarylated boranes, use thereof as organically semiconductor transmitters and/or transport materials, methods for producing same and uses thereof

1. A K type of copolyarylborane:

wherein:

hydrogen atoms are bonded to the ends;

Ar n represents at least one of Ar 1 , Ar 2 , and Ar 3 ;

Wherein Ar 1 and Ar 2 , independent of each other, are selected from mono (homo)aromatic arylenes, and polycyclic heteroaromatic arylenes; Ar 3 represents an heteroaromatic arylene radical; and each of Ar 1 , Ar 2 , and Ar 3 is bonded in the K type of copolyarylborane in a bivalent conjugating manner;

Ar 1 has π electron density of no less than that of benzene;

Ar 2 is capable of hole transport;

Ar 3 has a π electron density of no greater than that of benzene and less than that of Ar 1 ;

wherein Ar 1 is different from Ar 2 and Ar 3 and wherein Ar 2 is different from Ar 3 ;

x, y, and z respectively represent the molar parts of Ar 1 , Ar 1 , and Ar 3 ; each of x, y,

and z is in the range of 0-1, and x+y+z=1, wherein two of x, y, and z are not equal to 0; and

depending on the intended conjucation in the K type of copolyarylborane, R represents one of the following radicals:

(1) a heteroaromatic or a (homo)aromatic aryl radical, which is donor-free, wherein R's conjugation in the copolyarylborane is formed by application of an electrical field;

(2) a heteroaromatic or a (homo)aromatic aryl in which at least one additional donor function is substituted (intrinsic formation of conjugation); and

(3) a heteroaromatic or a (homo)aromatic aryl whose hydrogen atom(s) is substituted by one or more branched or unbranched alkyl radicals or alkoxy radicals R*.

2. The copolyarylborane of claim 1 wherein at least one of Ar n and R is substituted at an ortho position of a boron-carbon bond.

3. The copolyarylborane of claim 2 wherein at least one ortho substituent is a methyl substituent or a 3,6-durylene substituent arranged between a boron atom and an arylene radical.

4. The copolyarylborane of claim 1 wherein the copolyarylborane is one of the following compounds:

5. The copolyarylborane of claim 1 wherein Ar 1 has a 2,7-fluorenylene structure.

6. The copolyarylborane of claim 5 wherein the 2,7-fluorenylene structure is substituted in the 9 position by an unbranched or branched alkyl radical.

7. The copolyarylborane of claim 1 wherein Ar 1 is selected from the compounds of the Ar 1 (a-h) types shown in Table 1:

TABLE 1

Ar 1 (a1)

1,4-phenylene

Ar 1 (a2)

1,3-phenylene

Ar 1 (b1) 1,1′-

(4,4′-biphenylene)

Ar 1 (b2) 1,1′-(3,3′-

biphenylene)

Ar 1 (b3) 1,1′-(3,4′-

biphenylene)

Ar 1 (c)

2,7-fluorenylene

Ar 1 (d)

2,5-thienylene

Ar 1 (e) 2,2′-(5,5′-

bisthienylene)

Ar 1 (f1) 4′,5-(2-

phenylthienylene)

Ar 1 (f2) 3′,5-(2-

phenylthienylene)

Ar 1 (g1)

1,4-naphthylene

Ar 1 (g2)

1,5-naphthylene

Ar 1 (h1)

1,4-anthrylene

Ar 1 (h2)

9,10-anthrylene

Ar 1 (h3) 4′,4′-bis-

(9,10-diphenyl)-

anthrylene

where R* represents a branched or unbranched alkyl or alkoxy radical.

8. The copolyarylborane of claim 1 wherein Ar 2 has a perarylated amine substituent attached in a conjugating manner.

9. The copolyarylborane of claim 1 wherein Ar 2 is selected from the compounds of the Ar 2 (a-f) types shown in Table 2:

TABLE 2

Ar 2 (a)

[bis(2,2′diarylamino-3,3′-diaryl-5,5′thiene)]-4,4′-ylene

Ar 2 (b)

[N,N′-bis(thien-2-yl)- or N,N′-bis-(1,3-thiazol-2-yl)-

N,N′-diaryldiaminoarylene]-5,5′-ylene

Ar 2 (c)

[bis(2,2′-diarylamino)-3,3′-diaryl-4,4′-thienyl)arylene]-

5,5′-ylene

Ar 2 (d)

[N,N′-bis(3-duryl)-N,N′-diaryldiaminoarylene]-6,6′-ylene

Ar 2 (e)

Bis[(5,5-diarylaminophenyl)arlene]-2,2′-ylene

Ar 2 (f)

bis(4,4′-diarylaminophenyl) 2,2′-ylene

wherein R 2 , R 3 and R 4 are aryl substituents; R 1 is a substituent having the same definition as applied to Ar 1 in claim 1 ; and x is N or C—R 4 .

10. The copolyarylborane of claim 9 wherein the substituents R 2 , R 3 and R 4 are selected from the group consisting of phenyl, 1-naphthyl and 2-naphthyl.

11. The copolyarylborane of claim 9 wherein R 1 is one of Ar 1 as shown in table 2 of claim 9 .

12. The copolyarylborane of claim 9 wherein R 1 is selected from the group consisting of 9,9-dialkyl-2,7-fluorenylene and 3,6-durylene.

13. The copolyarylborane of claim 1 wherein Ar 3 is selected from the compounds of the Ar 3 (a-m) types shown in Table 3:

TABLE 3

Ar 3 (a1)

2,6-(diarylene)pyridinylenes

Ar 3 (a2)

2,5-(diarylene)pyridinylenes

Ar 3 (b)

2,5-(diarylene)pyrazinylenes

Ar 3 (c) 3,6-(diarylene)-1,2,4-

triazinylenes

Ar 3 (d1)

1,4-(diarylene)phthalazinylenes

Ar 3 (d2)

2,3-(diarylene)quinoxalinylenes

Ar 3 (d3)

1,4-(diarylene)phenazinylenes

Ar 3 (e)

1,4-(diarylene)benzo-

thiadiazolylenes

Ar 3 (f)

3,9-(diarylene)-1,7-diaza-

chrysenylenes

Ar 3 (g1)

bis(2,2′-(diarylene)-

pyrimidin-5,5′-ylene)arylenes

Ar 3 (g2)

2,2-pyrimidine-5,5-

(diarylene)-ylenes

Ar 3 (h)

bis[5,5′-(diarylene)-

pyrimidin-2,2′-ylene]arylenes

Ar 3 (i1)

2,2′-(5,5′-bis-1,3-

thiazolylenes)

Ar 3 (i2)

2,2′-(5,5′arylenebis-1,3-

thiazolylenes)

Ar 3 (j1)

5,5′-bis[2,5-(di-2′,2′-

thienyl)oxadiazolylenes]

Ar 3 (j2)

5,5′-bis(2,5-(di-2′,2′-

thienyl)thiadiazolylenes]

Ar 3 (k1)

4′,4′-bis(2,5-diphenyl-

oxadiazolylenes)

Ar 3 (k2)

4′,4′-bis(2,5-diphenyl-

thiadiazolylenes)

Ar 3 (l1)

2,2′-(5,5′-arylenebis-1,3-

thiazolylene)arylenes

Ar 3 (l2)

2,2′-(5,5′arylenebis-1,3-

thiazolylenes)

Ar 3 (m1)

4-(2,2′arylenebis-1,3-

thiazolylene)arylenes

Ar 3 (m2)

4,4′-(5,5′ylenebis-1,3-

thiazolylene)arylenes

wherein R 1 is a substituent having the same definition as applied to Ar 1 in claim 1 , and R* is a branched or unbranched alkyl or alkoxy radical.

14. The copolyarylborane of claim 1 wherein R is selected from the compounds of the types shown in Table 4:

TABLE 4

R(a1)

mesityl

R(a2) pen-

tamethylphenyl

R(a3)

1-naphthyl

R(a4)

2-naphthyl

R(a5)

3-alkyl/alkoxydur-

6-yl

R(b1)

2-diphenylamino

3,4-diphenylthien-

5-yl

R(b2)

2-(1-naphthyl)-

phenylamino] 3,4-

diphenylthien-5-yl

R(b3)

2-(N-carbazoyl)

3,4-dipheny]thien-

5-yl

R(c1)

2-diphenylamino

3,4-diphenyl-1,3-

thiazol-5-yl

R(c2)

2-[(1-naphthyl)-

phenylamino]-3,4

diphenyl-1,3

thiazol-5-yl

R(d1)

3-diphenylamino-

dur-6-yl

R(d2)

3-[(1-naphthyl)-

phenylamino]dur-6-

yl

R(d3)

3-(N-carbazoyl)-

dur-6-yl

R(e1)

2-diphenylamino-

3,4-diphenyl-5-(3-

dur-6-yl)thiophene

R(e2)

2-[(1-naphthyl)-

phenylamino]-3,4

diphenyl-5-(3-dur-

6-yl)thiophene

R(f)

N-carbazoyl

wherein R* represents a branched or unbranched alkyl or alkoxy radical; R(a1-a5) is donor free; and R(b-e) has at least one donor function substituted.

15. The copolyarylborane of claim 1 wherein the of the copolyarylborane in organic solvents is improved by an additional arrangement of one or more unbranched and/or branched alkyl substituents and/or alkoxy substituents R*.

16. The copolyarylborane of claim 15 wherein one or more of the alkyl substituents have from 1 to 10 carbon atoms.